Correction to synthesis and palladium-catalyzed coupling reactions of enantiopure p-bromophenyl methyl sulfoximine (Journal of Organic Chemistry (2005) 70, (2346) DOI: 10.1021/jo047940c);Synthesis and palladium-catalyzed coupling reactions of enantiopure p-bromophenyl methyl sulfoximine

Journal of Organic Chemistry

Volumn 70, Issue 6, 2005, Pages 2346-2349

  Gae, Young Cho ^a   Okamura, Hiroaki ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL MODIFICATION; DERIVATIVES; NITROGEN COMPOUNDS; PALLADIUM; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ARYL GROUPS; COUPLING REACTIONS; O-MESITYLENESULFONYLHYDROXYLAMINE (MSH); REACTION SEQUENCES;

AROMATIC COMPOUNDS;

4 BROMOPHENYLMETHYLSULFINATE; 4 BROMOPHENYLMETHYLSULFOXIMINE; HYDROXYLAMINE; IMINE; O MESITYLENESULFONYLHYDROXYLAMINE; PALLADIUM; SULFINIC ACID DERIVATIVE; TRIPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL MODIFICATION; STEREOSPECIFICITY; STILLE REACTION; SUBSTITUTION REACTION; SUZUKI REACTION;

EID: 15444368954     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902416n     Document Type: Erratum

References (63)

1. Reviews: (a) Okamura, H.; Bolm, C. Chem. Lett. 2004, 33, 482. (b) Harmata, M. Chemtracts 2003, 16, 660.
2. Reviews: (a) Okamura, H.; Bolm, C. Chem. Lett. 2004, 33, 482. (b) Harmata, M. Chemtracts 2003, 16, 660.
3. For recent representative examples, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321. (c) Bolm, C.; Martin, M.; Simic, O.; Verruci, M. Org. Lett. 2003, 5, 427. (d) Bolm, C.; Verruci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2816. (e) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M. P.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222. (f) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
4. For recent representative examples, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321. (c) Bolm, C.; Martin, M.; Simic, O.; Verruci, M. Org. Lett. 2003, 5, 427. (d) Bolm, C.; Verruci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2816. (e) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M. P.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222. (f) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
5. For recent representative examples, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321. (c) Bolm, C.; Martin, M.; Simic, O.; Verruci, M. Org. Lett. 2003, 5, 427. (d) Bolm, C.; Verruci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2816. (e) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M. P.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222. (f) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
6. For recent representative examples, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321. (c) Bolm, C.; Martin, M.; Simic, O.; Verruci, M. Org. Lett. 2003, 5, 427. (d) Bolm, C.; Verruci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2816. (e) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M. P.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222. (f) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
7. For recent representative examples, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321. (c) Bolm, C.; Martin, M.; Simic, O.; Verruci, M. Org. Lett. 2003, 5, 427. (d) Bolm, C.; Verruci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2816. (e) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M. P.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222. (f) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
8. For recent representative examples, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321. (c) Bolm, C.; Martin, M.; Simic, O.; Verruci, M. Org. Lett. 2003, 5, 427. (d) Bolm, C.; Verruci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2816. (e) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M. P.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222. (f) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
9. (a) Bolm, C.; Kahmann, J. D.; Moll, G. Tetrahedron Lett. 1997, 38, 1169.
10. (b) Bolm, C.; Moll, G.; Kahmann, J. D. Chem. Eur. J. 2001, 7, 1118.
11. (c) Tye, H.; Skinner, C. L. Helv. Chim. Acta 2002, 85, 3272.
12. (d) Bolm, C.; Müller, D.; Hackenberger, C. P. R. Org. Lett. 2002, 4, 893.
13. (e) Bolm, C.; Müller, D.; Dalhoff, C.; Hackenberger, C. P. R.; Weinhold, E. Bioorg. Med. Chem. Lett. 2003, 13, 3207.
14. (f) In this context, see also: Hackenberger, C. P. R.; Schiffers, I.; Runsink, J.; Bolm, C. J. Org. Chem. 2004, 69, 739.
15. For very early work in this area, see: (a) Mock, W. L.; Tsay, J.-T. J. Am. Chem. Soc. 1989, 111, 4467. (b) Mock, W. L.; Zhang, J. Z. J. Biol. Chem. 1991, 266, 6393.
16. For very early work in this area, see: (a) Mock, W. L.; Tsay, J.-T. J. Am. Chem. Soc. 1989, 111, 4467. (b) Mock, W. L.; Zhang, J. Z. J. Biol. Chem. 1991, 266, 6393.
17. Reviews: (a) Reggelin, M.; Zur, C. Synthesis 2000, 1. (b) Mikolajczk, M.; Drabowicz, J.; Kielbasinski, P. Chiral Sulfur Reagents; CRC Press: Boca Raton, 1997. (c) Pyne, S. Sulfur Rep. 1992, 12, 57. (d) Haake, M. In Houben-Weyl; Klamann, D., Eds.; VCH Thieme: Stuttgart, 1985; Vol. E11, p 1299. (e) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341. (f) Johnson, C. R. Aldrichim. Acta 1985, 18, 3.
18. Reviews: (a) Reggelin, M.; Zur, C. Synthesis 2000, 1. (b) Mikolajczk, M.; Drabowicz, J.; Kielbasinski, P. Chiral Sulfur Reagents; CRC Press: Boca Raton, 1997. (c) Pyne, S. Sulfur Rep. 1992, 12, 57. (d) Haake, M. In Houben-Weyl; Klamann, D., Eds.; VCH Thieme: Stuttgart, 1985; Vol. E11, p 1299. (e) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341. (f) Johnson, C. R. Aldrichim. Acta 1985, 18, 3.
19. Reviews: (a) Reggelin, M.; Zur, C. Synthesis 2000, 1. (b) Mikolajczk, M.; Drabowicz, J.; Kielbasinski, P. Chiral Sulfur Reagents; CRC Press: Boca Raton, 1997. (c) Pyne, S. Sulfur Rep. 1992, 12, 57. (d) Haake, M. In Houben-Weyl; Klamann, D., Eds.; VCH Thieme: Stuttgart, 1985; Vol. E11, p 1299. (e) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341. (f) Johnson, C. R. Aldrichim. Acta 1985, 18, 3.
20. Reviews: (a) Reggelin, M.; Zur, C. Synthesis 2000, 1. (b) Mikolajczk, M.; Drabowicz, J.; Kielbasinski, P. Chiral Sulfur Reagents; CRC Press: Boca Raton, 1997. (c) Pyne, S. Sulfur Rep. 1992, 12, 57. (d) Haake, M. In Houben-Weyl; Klamann, D., Eds.; VCH Thieme: Stuttgart, 1985; Vol. E11, p 1299. (e) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341. (f) Johnson, C. R. Aldrichim. Acta 1985, 18, 3.
21. Reviews: (a) Reggelin, M.; Zur, C. Synthesis 2000, 1. (b) Mikolajczk, M.; Drabowicz, J.; Kielbasinski, P. Chiral Sulfur Reagents; CRC Press: Boca Raton, 1997. (c) Pyne, S. Sulfur Rep. 1992, 12, 57. (d) Haake, M. In Houben-Weyl; Klamann, D., Eds.; VCH Thieme: Stuttgart, 1985; Vol. E11, p 1299. (e) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341. (f) Johnson, C. R. Aldrichim. Acta 1985, 18, 3.
22. Reviews: (a) Reggelin, M.; Zur, C. Synthesis 2000, 1. (b) Mikolajczk, M.; Drabowicz, J.; Kielbasinski, P. Chiral Sulfur Reagents; CRC Press: Boca Raton, 1997. (c) Pyne, S. Sulfur Rep. 1992, 12, 57. (d) Haake, M. In Houben-Weyl; Klamann, D., Eds.; VCH Thieme: Stuttgart, 1985; Vol. E11, p 1299. (e) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341. (f) Johnson, C. R. Aldrichim. Acta 1985, 18, 3.
23. (a) Fusco, R.; Tericoni, F. Chem. Ind. (Milan) 1965, 47, 61.
24. (b) Johnson. C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1973, 95, 7418.
25. (c) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424.
26. (d) Shiner, C. S.; Berks, A. H. J. Org. Chem. 1988, 53, 5542.
27. (e) Brandt, J.; Gais, H. J. Tetrahedron: Asymmetry 1997, 8, 909.
28. (a) Tamura, Y.; Minamikawa, J.; Sumoto, K.; Fujii, S.; Ikeda, M. J. Org. Chem. 1973, 38, 1239.
29. (b) Johnson, C. R.; Kirchhoff, R. A.; Corkins, H. G. J. Org. Chem. 1974, 39, 2458.
30. (c) Tamura, Y.; Matushima, H.; Minamikawa, J.; Ikeda, M.; Sumoto, K. Tetrahedron 1975 31, 3035.
31. Cu salts: (a) Müller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805. (b) Lacôte, E.; Amatore, M.; Fensterbank, L.; Malacria, M. Synlett 2002, 116. (c) Cren, S.; Kinahan, T. C.; Skinner, C. L.; Tye, H. Tetrahedron Lett. 2002, 43, 2749. (d) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2003, 85, 3773. (e) Takada, H.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 1999, 38, 1288. Fe salts: (f) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (g) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (h) Bolm, C.; Kesselgruber, M.; Muñiz, K.; Raabe, G. Organometallics 2000, 19, 1648. (i) Nakayama, J.; Otani, T.; Sugihara, Y.; Sano, Y.; Ishii, A.; Sakamoto, A. Heteroatom Chem. 2001, 12, 333. Rh complexes: (j) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305.
32. Cu salts: (a) Müller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805. (b) Lacôte, E.; Amatore, M.; Fensterbank, L.; Malacria, M. Synlett 2002, 116. (c) Cren, S.; Kinahan, T. C.; Skinner, C. L.; Tye, H. Tetrahedron Lett. 2002, 43, 2749. (d) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2003, 85, 3773. (e) Takada, H.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 1999, 38, 1288. Fe salts: (f) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (g) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (h) Bolm, C.; Kesselgruber, M.; Muñiz, K.; Raabe, G. Organometallics 2000, 19, 1648. (i) Nakayama, J.; Otani, T.; Sugihara, Y.; Sano, Y.; Ishii, A.; Sakamoto, A. Heteroatom Chem. 2001, 12, 333. Rh complexes: (j) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305.
33. Cu salts: (a) Müller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805. (b) Lacôte, E.; Amatore, M.; Fensterbank, L.; Malacria, M. Synlett 2002, 116. (c) Cren, S.; Kinahan, T. C.; Skinner, C. L.; Tye, H. Tetrahedron Lett. 2002, 43, 2749. (d) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2003, 85, 3773. (e) Takada, H.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 1999, 38, 1288. Fe salts: (f) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (g) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (h) Bolm, C.; Kesselgruber, M.; Muñiz, K.; Raabe, G. Organometallics 2000, 19, 1648. (i) Nakayama, J.; Otani, T.; Sugihara, Y.; Sano, Y.; Ishii, A.; Sakamoto, A. Heteroatom Chem. 2001, 12, 333. Rh complexes: (j) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305.
34. Cu salts: (a) Müller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805. (b) Lacôte, E.; Amatore, M.; Fensterbank, L.; Malacria, M. Synlett 2002, 116. (c) Cren, S.; Kinahan, T. C.; Skinner, C. L.; Tye, H. Tetrahedron Lett. 2002, 43, 2749. (d) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2003, 85, 3773. (e) Takada, H.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 1999, 38, 1288. Fe salts: (f) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (g) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (h) Bolm, C.; Kesselgruber, M.; Muñiz, K.; Raabe, G. Organometallics 2000, 19, 1648. (i) Nakayama, J.; Otani, T.; Sugihara, Y.; Sano, Y.; Ishii, A.; Sakamoto, A. Heteroatom Chem. 2001, 12, 333. Rh complexes: (j) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305.
35. Cu salts: (a) Müller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805. (b) Lacôte, E.; Amatore, M.; Fensterbank, L.; Malacria, M. Synlett 2002, 116. (c) Cren, S.; Kinahan, T. C.; Skinner, C. L.; Tye, H. Tetrahedron Lett. 2002, 43, 2749. (d) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2003, 85, 3773. (e) Takada, H.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 1999, 38, 1288. Fe salts: (f) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (g) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (h) Bolm, C.; Kesselgruber, M.; Muñiz, K.; Raabe, G. Organometallics 2000, 19, 1648. (i) Nakayama, J.; Otani, T.; Sugihara, Y.; Sano, Y.; Ishii, A.; Sakamoto, A. Heteroatom Chem. 2001, 12, 333. Rh complexes: (j) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305.
36. Cu salts: (a) Müller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805. (b) Lacôte, E.; Amatore, M.; Fensterbank, L.; Malacria, M. Synlett 2002, 116. (c) Cren, S.; Kinahan, T. C.; Skinner, C. L.; Tye, H. Tetrahedron Lett. 2002, 43, 2749. (d) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2003, 85, 3773. (e) Takada, H.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 1999, 38, 1288. Fe salts: (f) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (g) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (h) Bolm, C.; Kesselgruber, M.; Muñiz, K.; Raabe, G. Organometallics 2000, 19, 1648. (i) Nakayama, J.; Otani, T.; Sugihara, Y.; Sano, Y.; Ishii, A.; Sakamoto, A. Heteroatom Chem. 2001, 12, 333. Rh complexes: (j) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305.
37. Cu salts: (a) Müller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805. (b) Lacôte, E.; Amatore, M.; Fensterbank, L.; Malacria, M. Synlett 2002, 116. (c) Cren, S.; Kinahan, T. C.; Skinner, C. L.; Tye, H. Tetrahedron Lett. 2002, 43, 2749. (d) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2003, 85, 3773. (e) Takada, H.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 1999, 38, 1288. Fe salts: (f) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (g) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (h) Bolm, C.; Kesselgruber, M.; Muñiz, K.; Raabe, G. Organometallics 2000, 19, 1648. (i) Nakayama, J.; Otani, T.; Sugihara, Y.; Sano, Y.; Ishii, A.; Sakamoto, A. Heteroatom Chem. 2001, 12, 333. Rh complexes: (j) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305.
38. Cu salts: (a) Müller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805. (b) Lacôte, E.; Amatore, M.; Fensterbank, L.; Malacria, M. Synlett 2002, 116. (c) Cren, S.; Kinahan, T. C.; Skinner, C. L.; Tye, H. Tetrahedron Lett. 2002, 43, 2749. (d) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2003, 85, 3773. (e) Takada, H.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 1999, 38, 1288. Fe salts: (f) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (g) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (h) Bolm, C.; Kesselgruber, M.; Muñiz, K.; Raabe, G. Organometallics 2000, 19, 1648. (i) Nakayama, J.; Otani, T.; Sugihara, Y.; Sano, Y.; Ishii, A.; Sakamoto, A. Heteroatom Chem. 2001, 12, 333. Rh complexes: (j) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305.
39. Cu salts: (a) Müller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805. (b) Lacôte, E.; Amatore, M.; Fensterbank, L.; Malacria, M. Synlett 2002, 116. (c) Cren, S.; Kinahan, T. C.; Skinner, C. L.; Tye, H. Tetrahedron Lett. 2002, 43, 2749. (d) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2003, 85, 3773. (e) Takada, H.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 1999, 38, 1288. Fe salts: (f) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (g) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (h) Bolm, C.; Kesselgruber, M.; Muñiz, K.; Raabe, G. Organometallics 2000, 19, 1648. (i) Nakayama, J.; Otani, T.; Sugihara, Y.; Sano, Y.; Ishii, A.; Sakamoto, A. Heteroatom Chem. 2001, 12, 333. Rh complexes: (j) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305.
40. Cu salts: (a) Müller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805. (b) Lacôte, E.; Amatore, M.; Fensterbank, L.; Malacria, M. Synlett 2002, 116. (c) Cren, S.; Kinahan, T. C.; Skinner, C. L.; Tye, H. Tetrahedron Lett. 2002, 43, 2749. (d) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2003, 85, 3773. (e) Takada, H.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 1999, 38, 1288. Fe salts: (f) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015. (g) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. (h) Bolm, C.; Kesselgruber, M.; Muñiz, K.; Raabe, G. Organometallics 2000, 19, 1648. (i) Nakayama, J.; Otani, T.; Sugihara, Y.; Sano, Y.; Ishii, A.; Sakamoto, A. Heteroatom Chem. 2001, 12, 333. Rh complexes: (j) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305.
41. Cho, G. Y.; Bolm, C. Unpublished results.
42. Reviews: (a) Kagan, H. B.; Luukas, T. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004; p 479. (b) Kagan, H. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Eds.; Wiley-VCH: New York, 2000; p 327. (c) Bolm, C.; Muñiz, K.; Hildebrand, J. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 697.
43. Reviews: (a) Kagan, H. B.; Luukas, T. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004; p 479. (b) Kagan, H. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Eds.; Wiley-VCH: New York, 2000; p 327. (c) Bolm, C.; Muñiz, K.; Hildebrand, J. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 697.
44. Reviews: (a) Kagan, H. B.; Luukas, T. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004; p 479. (b) Kagan, H. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Eds.; Wiley-VCH: New York, 2000; p 327. (c) Bolm, C.; Muñiz, K.; Hildebrand, J. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 697.
45. (a) Capozzi, M. A. M.; Cardellicchio, C.; Naso, F.; Spina, G.; Tortorella, P. J. Org. Chem. 2001, 66, 5933.
46. (b) For a review, see: Capozzi, M. A. M.; Cardellicchio, C.; Naso, F. Eur. J. Org. Chem. 2004, 1855.
47. (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
48. (b) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000; p 195.
49. (c) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051.
50. (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
51. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
52. (c) Stanforth, S. P. Tetrahedron 1998, 54, 263.
53. (d) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
54. (e) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
55. (f) Bellina, F.; Carpita, A.; Rossi, R. Synthesis 2004, 2419.
56. (g) See also: Miura, M. Angew. Chem., Int. Ed. 2004, 43, 2201 and references therein.
57. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
58. (b) Farina, V.; Krishnamurthy, V.; Scott, W. Org. React. 1997, 50, 1.
59. (c) Handy, S. T.; Zhang, X. Org. Lett. 2001, 3, 233.
60. (d) Mitchel, T. N. In Metal Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 167 and references therein.
61. 3).
62. Hackenberger, C. P. R.; Raabe, G.; Bolm, C. Chem. Eur. J. 2004, 10, 2942.
63. HBTU: O-Benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate. EEDQ: 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline ethyl 1,2-dihydro-2-ethoxy-1-quinolinecarboxylate.